| Identification | More | [Name]
Cupferron | [CAS]
135-20-6 | [Synonyms]
AMMONIUM NITROSOPHENYLHYDROXYLAMINE
AMMONIUM-N-NITROSOPHENYL-HYDROXYLAMINE
AMMONIUM SALT OF NITROSOPHENYLHYDROXYLAMINE
COPPERONE
CUPFERRON
N-HYDROXY-N-NITROSOBENZENAMINE AMMONIUM SALT
NITROPHENYLHYDROXYLAMINE AMMONIUM
NITROSOPHENYLHYDROXYLAMINE AMMONIUM SALT
N-NITROSO-N-PHENYLHYDROXYAMINE AMMONIUM SALT
N-NITROSO-N-PHENYLHYDROXYLAMINE
N-NITROSO-N-PHENYLHYDROXYLAMINE, AMMONIUM DERIVATIVE
N-NITROSO-N-PHENYLHYDROXYLAMINE AMMONIUM SALT
N-NITROSO-N-PHENYLHYDROXYLAMINE NH3
N-NITROSOPHENYLHYDROXYLAMINE AMMONIUM SALT
N-PHENYL-N-NITROSOHYDROXYLAMINE AMMONIUM SALT
AminoniumN-nitrosophenylhydroxylamine
Ammonium cupferron
ammoniumcupferron
ammoniumnitroso-beta-phenylhydroxylamine
Benzenamine, N-hydroxy-N-nitroso-, ammonium salt | [EINECS(EC#)]
205-183-2 | [Molecular Formula]
C6H9N3O2 | [MDL Number]
MFCD00078422 | [Molecular Weight]
155.15 | [MOL File]
135-20-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Cupferron is a creamy-white crystalline compound | [Melting point ]
150-155 °C (dec.) (lit.) | [Boiling point ]
278.95°C (rough estimate) | [density ]
1.3092 (rough estimate) | [refractive index ]
1.6500 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
well soluble in water and ethanol. | [form ]
Powder | [color ]
Needles from water | [Stability:]
Stable, but may be moisture sensitive. Incompatible with strong oxidizing agents, strong bases, strong acids. | [Water Solubility ]
<0.1 g/100 mL at 18.5 ºC | [Merck ]
14,2622 | [BRN ]
3919107 | [InChIKey]
GDEBSAWXIHEMNF-UHFFFAOYSA-O | [CAS DataBase Reference]
135-20-6(CAS DataBase Reference) | [IARC]
2B (Vol. 127) | [NIST Chemistry Reference]
Cupferron(135-20-6) | [EPA Substance Registry System]
Cupferron (135-20-6) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R25:Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R40:Limited evidence of a carcinogenic effect.
R45:May cause cancer.
R43:May cause sensitization by skin contact.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S53:Avoid exposure-obtain special instruction before use . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
NC4725000
| [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29299090 | [Safety Profile]
Confirmed carcinogen
with experimental carcinogenic and
tumorigenic data. Poison by intravenous
route. An eye irritant. Solutions with
thorium salts are unstable explosives above
15°C. Solutions with titanium or zirconium
salts are unstable explosives above 40℃.
When heated to decomposition it emits very
toxic NH3 and NOx. See also N-NITROSO
COMPOUNDS and AMINES | [Hazardous Substances Data]
135-20-6(Hazardous Substances Data) | [Toxicity]
TDLo orl-rat: 123 g/kg/78W-C:CAR NCITR* NCI-CGTR-100,78 |
| Hazard Information | Back Directory | [General Description]
Light yellow or cream-colored crystals or a brown crystalline solid. As a reagent in the separation of copper and iron. | [Reactivity Profile]
CUPFERRON(135-20-6) may be sensitive to prolonged exposure to air. Incompatible with strong oxidizing agents, strong acids and strong bases. Forms unstable solutions with thorium, titanium and zirconium salts. | [Air & Water Reactions]
Hygroscopic. Soluble in water. | [Potential Exposure]
Cupferron is used to separate tin from zinc, and copper and iron from other metals in the laboratory. Cupferron also finds application as a quantitative reagent for vanadates and titanium; and for the colorimetric determination of aluminum. The potential for exposure appears to be greatest for those engaged in analytical or research studies involving use of the chemical. Workers may also be exposed to the compound during manufacturing processes. | [Fire Hazard]
Flash point data for this chemical are not available; however, CUPFERRON is probably combustible. | [First aid]
Move victim to fresh air. Call 911 or emergency Medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy. | [Shipping]
UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. | [Incompatibilities]
Forms unstable and possibly explosive compounds with thorium salts; titanium, zirconium. | [Description]
Cupferron is a creamy-white crystalline compound. Molecular weight=156.21; Freezing/Melting point=163℃. Hazard Identification (based on NFPA-704M Rating System): Health 2, Flammability 2, Reactivity 1.Soluble in water | [Carcinogenicity]
Cupferron is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals. | [storage]
Color Code—Green: General storage may be used.Color Code—Blue: Health Hazard/Poison: Store in a securepoison location. Prior to working with cupferron you shouldbe trained on its proper handling and storage. A regulated,marked area should be established where this chemical ishandled, used, or stored in compliance with OSHAStandard 1910.1045. Cupferron should be stored in a refrigerator or in a cool dry place and protected from exposure tomoisture. | [Purification Methods]
Recrystallise it twice from EtOH after treatment with Norite and finally once with EtOH. The crystals are washed with diethyl ether and air dried, then stored in the dark over solid ammonium carbonate. A standard solution (ca 0.05M prepared in air-free H2O) is prepared daily from this material for analytical work and is essentially 100% pure. [Olsen & Elving Anal Chem 26 1747 1954.] It can also be washed with Et2O, dried and stored as stated. In a sealed, dark container it can be stored for at least 12 months without deterioration. 260nm (CHCl3). max [Marvel Org Synth Coll Vol I 177 1941, Elving & Olson J Am Chem Soc 78 4206 1956, Beilstein 16 IV 891.] Possible CARCINOGEN. |
| Questions And Answer | Back Directory | [Analysis reagents]
Cupferron is an important analytical reagent, as Ammonium salt of N-nitroso hydroxylamine, commonly known as cupferron. It is usually white or light yellow bright flake scrystal, with sweet odour, long home to darken due to slow decomposition, but in fact can also be used in the analysis. It is soluble in water, benzene, alcohol, ether. The reagent is thermally decomposed to prepare nitrobenzene. Unstable in light and air, we need to save itin a brown reagent grinding mouth bottle, usually place a small amount of ammonium carbonate in bottle packaged with paper or cloth good as a preservative, store in a sealed dark cool place. It can be used as a precipitating agent and solvent extraction agent of copper, iron, tin, titanium, vanadium, chromium and other elements, as a masking agent for the determination of rare earth.
Nitrobenzene is reduced with zinc powder in an aqueous solution of ammonium chloride to get phenylhydroxylamine, which is then dissolved in ether, lead to excessive ammonia, and addn-butyl nitrite, then get cupferron, can form a stable five-membered ring chelate with metal ions, therefore, it is common organic precipitant. It can quantitatively measure Fe3 + ions in the acid solution, can also be measure Cu2 +, Sn4 +, Ti4 +, Ga3 +, Hf4 +and other ions, and vanadate (VO-3, VO3-3). When Fe3 +, Cu2 + ions mixedwith other metal ions together, the reagent can be used to separate them out. It is a chelating extractant for Al3 +, Au3 +, Be2 +, Co2 +, La3 +, Pu4 + and other ions, a masking agent for rare earth metal ions.
The above information is edited by the chemicalbook of Yan Yanyong.
| [Purification method]
Ddd 30g powdered crude into 120ml60 ℃ water, make it all dissolved, add 2g of powdered activated carbon and stir for 10~15min, filtrate with the calcined Buchner, and cool the filtrate to 10~15 ℃, then cool to 0 ℃ overnight. Suction filtration by using a glass filter to precipitate crystals, wash with 10ml ethanol and then wash with 10ml of ether, and dry in air.
Cupferron can also be recrystallized with ethanol to purify.
| [Chemical properties]
It is white or cream colored flaky crystals. Melting point is 163-164 ℃, it is soluble in water and alcohol.
| [Uses]
1. Cupferron is used for quantitative analysis for aluminum, zinc, copper, iron, gallium, mercury, manganese, niobium, tin, tantalum, thorium, titanium, vanadium, zirconium and other elements
2. It is used as polymerization inhibitor, due to unique polymerization inhibition characteristics of cupferron, also the amount is small, can be used as an alternative of phenol polymerization inhibitor BHT, which is current largely applicated.
3. Cupferron is used for colorimetric determination for the weight of aluminum, bismuth, copper, iron, mercury, zinc, manganese, niobium, gallium, tantalum, thorium, titanium, vanadium, tin and other elements of. It is used for quantitative determination of iron in the strong acid solution, quantitative analysis of vanadate, separation of copper and iron together with the other metals, as a masking agent for measuring rare earths. | [Production method]
Benzene hydroxylamine ether solution was cooled in an ice bath, lead to an excess of ammonia, while stirring and continue adding the ammonia, solution of n-butyl nitrite was added for about 1h, then stir for 15min. Filter precipitate of cupferron, wash with diethyl ether, dry to get products. The product should be stored in a brown glass bottle, the bottle is placed a small amount of ammonium carbonate wrapped by paper (or cloth) as a stabilizer.
| [Category]
Pesticide
| [Toxicity grading]
highly toxic
| [Acute toxicity]
oral-rat LD 50: 199 mg/kg, intravenous-Mouse LD50: 180 mg/kg
| [Irritation data]
Eye-rabbit 20 mg/24 hours moderate
| [Explosive hazardous properties]
Explosive with thorium salt, zirconium salt or titanium salt solution at room temperature
| [Flammability hazard characteristics]
It produces toxic fumes of nitrogen oxides and ammonia at high temperature.
| [Storage characteristics]
Treasury ventilation, low-temperature drying
| [Extinguishing agent]
Dry powder, foam, sand, carbon dioxide, water mist |
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